Anthelmintic feed composition



pounds. "class include 2,2 dihydroxy 5,5 dichlorodiphenylmethane, 2,2dihydroxy-5,5'-dibrQmQdi* Patented Mar. 13, 1951 UNITED STATES *PATENTOFFICE ;j*

ANTHELMINTIC FEED COMPOSITION Arthur Henry Craige, Jr., Riverdale, Md.,as-

signor, by mesne assignments, to The Dow Chemical Company, Midland,Mich., a corporation of Delaware No Drawing. Original applicationMay.8,1945,

Serial No. 592,729. Divided and this application October 6, 1949, SerialNo. 120,000

in which Y and Y represent phenyl radicals each having at least onehalogen substituent and at least one hydroxy substituent.

In accordance with the present invention, it

has been discovered that feed compositionscontaining in proper amounts*a compound-as illus-- trated by the above formula are extremelyefficient anthelmintics when consumed by animals or fowl infested withworms.

It is an advantage of the present invention that my compositions possessa high therapeutic index, i. e., a relatively low toxicity at theeffective anthelmintic doses.

While my compositions are generally useful for the control of internalparasitic infestations of the alimentary tract of stock and poultry, itis an advantage that they are especially eiiective in the treatment oftapeworm infestations.

The active ingredients of my feed compositions can broadly be classifiedas diphenylmethanes wherein each of the phenyl group contains at leastone halogen substituent and at least one hydroxy substituent. I havefound that at least one halogen substituent and at least one hydroxysubstituent must be present on the phenyl roups, on the other hand,other substituents, i. e., alkyl groups may also be present withoutdestroying their anthelmintic activity.

Included among the compounds useful in accordance with my invention arethose set forth hereinafter.

My preferred active ingredients are those compounds represented by thefollowing formula:

I I- o- HO OH in which X represents a halogen, selected from the groupconsisting of chlorine and bromine and n represents 1, 2, 3, or 4 andsalts of such com- Specific compounds falling within this 2phenylmethane, 2,2 dihydroxy 3,5,3',5'-tetrachlorodiphenylmetha'ne,2,2-dihydroxy-3,5,3',5'-

tetrabromodiphenylmethane, 2,2 dihydroxy 3,5,6,3',5,6'hexachlorodiphenylmethane, 2,2

dihydroxy r 3,4,5,6,3,4,5,6-octachlorodiphenyl-.i methane, 2,2dihydroxy-5,5-dibromo-3,6,3',6'-.

tetrachlorodiphenylmethane, 2,2 dihydroxy 3,5,6,3',5',6'hexabromodiphenylmethane,. andtheir salts including alkali metal,alkaline earth,"

metal, and heavy metal salts.

As previously indicated the phenyl'groups may have in addition to thehalogen and hydroxy groups on the ring an alkyl. group and still beuseful as additions tofeeds-tuffsin accordance Withmy n- :Amongisush alkl jsubs irituted compounds may beinclud'ed 2,2 "dlh ydroxy;

4,4 dimethyl 5,5'dichlorodiphenylunethantr 2,2 dihydroxy 4,4 -'dimethyl3,5 ,3.'.',5..+ t etrachlorodiphenylmethane, 2,2 '-:dihydroxy-4,4F-dimethyl 3,5,6,3',5,6' hexachlorodiphenylmeth: ane and related compoundshaving. the methyl group in some position other than-- 4 or in more thanone position as well as those wherein some or all of the chlorines arereplaced by bromine, and those wherein the methyl groups are replaced bya lower alkyl group such as ethyl, propyl, butyl or amyl.

Among those compounds having more than one hydroxy group on the phenylrings may be included 2,4,2',4' tetrahydroxy5,5'-dichlorodiphenylmethane, 2,4,6,2',4,6' heXahydroxy-5,5'-

dichlorodiphenylmethane, 2,4,2',4'-tetrahydroxy-3,5,3,5-tetrachlorodiphenylmethane and the corresponding bromocompounds.

It is to be distinctly understood that my feed compositions are usefulfor combating internal parasites of the gastrointestinal tract of anydomestic animal or fowl.

The percentage of active ingredient in my feed compositions can bevaried. It is only necessary that the active ingredient constitute aproportion such that an adequate dose will be obtained by the animalsconsuming the food. The amount can be varied from onl a fraction of apercent to several percent. For example, a poultry mash containing 0.1%can be effectively employed or one containing 10% can be effectivelyemployed.

It is obvious that the preceding descriptions are intended to beillustrative only and they may be varied or modified to a considerableextent without departing from the spirit of the invention or sacrificingthe advantages thereof. I do not, therefore, intend to limit myinvention to the specific embodiments herein set forth except asindicated in the appended claims.

3 This application is a division of my co-pending application, Ser. No.592,729, filed May 8, 1945.

My feed compositions are prepared by mixing the diphenylmethane with anysuitable animal feed or feed con'centrate,

Having thus described my invention, Iolaim: 1., A poultry feedcontaining from 0.1% to 10% of2,2-dihydroxy-5,5'-dichlorodiphenylmethane:

2. A poultry feed containing from0;1 %=to l0% of2,2'-dihydroxy-5,5'-dibromodiphenylmethane.

3. A poultry feed containingjronr 021% te-1e of 2,2 dihydroxy3,5,6,'3'i5';6'-hexachlorodi phenylmethane.

4. An animal and. poultry feed containing a minor proportion of asubstance;representclzby;

the following formula:

in which X represents a Halogen selected from: the group'- consistingof" chlorine and: bromine, saidhalogen su'listi'tnents being arrangedsym metrically, and-'n represents a whole integerof thegroupconsisting'of 1; 2," 3Yancl4: I

An animal and poultry feed containing. a minor proportion of 'a"sub'stance representedz by. thefollowing formula:

iii-which the chlorine suhstituents: are: arranged symmetrically,- and nrepresenting; whole integerof 'the' group? consistingrroffr, 2, mane-4;

\An animal and;- poultryfeedi containing: a;- minor' pr'oporitiom of "a;substance represented: by. the foilowing'iormularin which the brominesubstituents are arranged symmetrically, and n represents a wholeinteger of the group consisting of 1, 2, 3, and 4.

7. A medicated poultry and animal feed effective'in themontrol. ofinternal parasites, containingaminor proportionof"2,2-dihydroxy-5,5'-di- 1 chlorodiphenylmethane.

8. A medicated poultry and animal feed effectivedn-rther control ofinternal parasites containing a minor proportion of2,2-dihydroxy-5,5'-dibromodiphenylmethane.

93 A medicated poultry and animal feed effec-- tive' in the; control ofinternal parasites containing a minor' proportion of 2,2'-dihydroxy-3:,5i63 i5'.fi-hexachlorodiphenylmethane.

ARTHUR, HENRY CRAIGE, JR.

REFERENCES CITED The following references are of record in the filetofthis patent UNITED STATES EATENTS- C'ade: Soap and. Sanitary Chemicals,yolume 20.,- Feb. 1944, pages 111 to 1,151.

4. AN ANIMAL AND POULTRY FEED CONTAINING A MINOR PROPORTION OF ASUBSTANCE REPRESENTED BY THE FOLLOWING FORMULA: